The use of DFT methods to predict the reduction potential of chalcones

This study explores the relationship between electronic structure and redox properties of a series of chalcone derivatives using density functional theory (DFT). The geometries of both neutral and one-electron-reduced chalcones were optimized, and various electronic descriptors were computed, including frontier molecular orbital energies, energy differences (Δ E , Δ G ), electron affinity, chemical potential, and electrophilicity indices. These descriptors were systematically correlated with experimentally determined reduction potentials measured in DMF versus the ferrocene/ferrocenium (Fc/Fc + ) reference. The results reveal strong linear relationships, particularly for para -substituted and ortho -OH-substituted chalcones, enabling reliable prediction of reduction behavior based on DFT-derived properties. Structural analysis also highlighted changes in planarity upon reduction, providing insight into conjugation and electron delocalization effects. Overall, the study demonstrates the utility of DFT-based methods for understanding and predicting redox characteristics in conjugated organic systems. DFT prediction of chalcone redox behavior. • DFT used to model neutral and reduced chalcone geometries and energies • Electronic descriptors correlate linearly with experimental redox potentials • Ortho -OH and para -substituted chalcones show distinct reduction trends • Reduction enhances planarity, promoting conjugation across the molecule • DFT enables prediction of chalcone redox behavior in DMF vs. Fc/Fc +